Old Town Winchester
Winchester
Visit Old Town Winchester
Popular places to visit
Handley Regional Library
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Visit the cosy cafes or top-notch restaurants in this walkable area.
Museum of the Shenandoah Valley
You can spend time browsing the exhibits at Museum of the Shenandoah Valley during your trip to Winchester. Visit the cosy cafes or top-notch restaurants in this walkable area.
Shenandoah Valley Discovery Museum
You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savour the top-notch restaurants.
Bright Box Theater
Enjoy a performance at Bright Box Theater, a popular theatre in Winchester. While in this walkable area, you can savour the top-notch restaurants.
Old Court House Civil War Museum
You can study the exhibits at Old Court House Civil War Museum, a museum with a story of its own, during your trip to Winchester. While in this walkable area, you can savour the top-notch restaurants.
George Washington's Office
You can find out about the history of Winchester with a visit to George Washington's Office. While in this walkable area, you can savour the top-notch restaurants.
Things to do
Shenandoah Tour: Self-Guided Drive
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
Staff was amazing! Benjamin and Carla are two of the kindest people ever!
Reviewed on 4 Jan, 2026
Microtel Inn & Suites by Wyndham Winchester
The poor: (1) lights were difficult to figure out as multiple switches had to be used; (2) breakfast of a cold, rubbery fried egg was very subpar; The good: (1) very clean! (2) great coffee for breakfast, (3) bed was very comfortable esp. pillows.
Reviewed on 31 Dec, 2025
La Quinta Inn & Suites by Wyndham Winchester
Great
Reviewed on 4 Jan, 2026
Travelodge by Wyndham Winchester
All of the above mentioned and a great, nutritious and varied breakfast. Also, both regular and decaf coffee were available in the breakfast area whenever I wanted it. Lastly, plentiful parking.
Reviewed on 27 Dec, 2025
Comfort Inn & Suites Winchester
We stayed twice,one night 2 weeks apart.The rooms on the parking lot side have a lot less outdoor noise, the rooms on the back of the building are against Interstate 81. We got very little sleep in the room against the highway because of constant noise from traffic. Always ask for an odd number room ...
Reviewed on 3 Jan, 2026
Quality Inn Winchester
Staff very friendly and courteous. Room very clean.
Reviewed on 1 Jan, 2026
Check Old Town Winchester hotel availability
Other neighbourhoods around Old Town Winchester
Winchester Historic District
While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.
